Soon after the NHL free agency window officially opened on Sunday, superstar centre John Tavares announced he was signing with his hometown Maple Leafs.

The seven-year, US$77-million deal, with an average annual value of $11 million against the salary cap, is one of the biggest free-agent acquisitions in the history of the city.

With that in mind, here’s a look at five of the biggest free-agent deals handed out by Toronto sports teams.

ROGER CLEMENS — FOUR-YEAR, US$40-MILLION CONTRACT WITH BLUE JAYS

The best free-agent signing in Blue Jays history is likely also one of the most successful by a Toronto club.

Roger Clemens inked a deal with team in 1996, following a succession of disappointing seasons with the Boston Red Sox. The then-33-year-old was four years removed from his last all-star appearance and had compiled a 40-39 record over the course of those campaigns.

But the “Rocket’s” tenure with the Jays proved to be a different story.

Clemens captured back-to-back American League Cy Young Awards, winning 21 games in the 1997 season and 20 the following year, with earned run averages of 2.05 and 2.65, respectively. He also won pitching’s equivalent of the Triple Crown by leading the AL in ERA, wins and strikeouts during both seasons.

Toronto was just three years removed from their back-to-back World Series titles, but during Clemens’ two-year stint with the Blue Jays, the team failed to make a playoff appearance. His time in Toronto ended on a sour note after he demanded a trade and wound up on the AL rival Yankees.

Clemens accomplishments have since been tarnished by his implication in the Mitchell Report on the use of performance-enhancing drugs in baseball.

It was billed as a “bloody big deal” by the club when it acquired English striker Jermain Defoe in a record-breaking MLS transfer fee in 2014. But it turned out to be more of a bloody mess.

On paper, the diminutive forward’s time with Toronto appeared to be a success: 11 goals in his first 16 games.

But Defoe struggled to stay on the field, as he never scored again and missed 12 of his next 18 games because of injury or suspension. Toronto also failed to make the playoffs for its eighth straight year.

When the then-32-year-old striker returned to England to rehab his injuries, rumours swirled about his future with the club and he was eventually sent to Sunderland in a deal that saw American forward Jozy Altidore head to Toronto FC.

The 12-time all-star and 1994 MVP was at the tail end of his career, but for a team that was inches away from a trip to the Eastern Conference finals off a Vince Carter buzzer-beater, Hakeem Olajuwon seemed as though he could be the final piece that put the Raptors over the hump.

The NBA champion and two-time Finals MVP was traded to Toronto in the 2001 off-season for a first- and second-round pick after he turned down a three-year, $13 million deal with the Rockets.

Despite the promise, Olajuwon, who was 38 at the time, struggled in Toronto, averaging a career-low 7.1 points and 6.0 rebounds per game and the Raptors failed to make it out of the first round of the playoffs.

Olajuwon retired after just one season with a back injury.

RAGHIB ISMAIL — FOUR-YEAR, US$18.2-MILLION CONTRACT

It was a coup unheard of at the time and likely never to happen again.

University of Notre Dame wide receiver Raghib Ismail, who was projected to be the first overall pick in the NFL Draft, opted instead to sign with the CFL’s Argonauts in 1991.

The stunning deal earned Ismail, who was 21 years old at the time, $4.55 million a season, when the league’s salary cap was merely $3 million. However, the majority of his salary was arranged as a personal services contract, so as to avoid these budgetary constraints.

The move paid fast dividends as Ismail made the 1991 all-star team, finished the season as runner-up for rookie of the year and clinched the Grey Cup for the Argos on an 87-yard kickoff return touchdown en route to winning MVP.

But it all fell apart the following season as Toronto missed the playoffs and the team’s majority owner, Bruce McNall, dealt with financial troubles. Ismail quit after the campaign and embarked on a nearly decade-long career in the NFL.

CURTIS JOSEPH — FOUR-YEAR, US$24-MILLION CONTRACT

Upon his arrival during the 1998 off-season, the Maple Leafs hadn’t made a playoff appearance since the 1995-96 campaign.

But that all changed, thanks in large part to Curtis Joseph. The then 31-year-old goalie helped the Leafs clinch a playoff berth in his first season with team, winning 35 games and posting a .910 save percentage along with a 2.56 goals-against average. Joseph also backstopped the Leafs to the Eastern Conference Final and was the runner-up to Dominik Hasek for the Vezina.

The following campaign, Joseph improved his stats, winning 36 games and putting up a .915 save percentage, on his way to being a finalist for the Vezina once again.

And in his final season with the club, “Cujo” pushed the Leafs to within two wins of making the Stanley Cup Final.

When his contract expired, Joseph signed with the Detroit Red Wings in hopes of finally winning a championship.

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